Azo dyestuffs



I Patented Nov. 28, 1933 t I V I r T D STA E P NT:

I 1,936,979 fAzo DYESTUFFS Erwin Hoffa, Frankfort-on-the-Main-Hoehst, and Eugen Glieten berg, Leverkusen, near Co logne, Germany, assignors 'to General Aniline Works, Inc., New York, N. Y., a corporation of .Delaware a No Drawing. Application September 28, 1928,

Serial No. 309,124, and in Germany October 13,1927 I a 1 I i v.

. '8 Claims. (01. 260-95) I I The present invention relates to new azo dyethus produced on the fiber has the 'following stufis and to fiber dyed therewith. struoturalformula:

We have found, that the diazo compounds of I the 2.5-dimethyl-4-ha1ogen-1-aniline are capa- 5' ble of yieldingdyestuffs of good fastness to light when. coupled with an arylamide of the 2-hydroxynaphthalene-3ecarboxylic acid. The new dyestuffs may also be produced on a substratum or on the fiber. I t The dyestuffs according to this invention are I I,

characterized by the formula: (2) By substituting for the 11.1 parts of 2-.hy-

droxynaphthalene-3-oarboxylic acidr-meth-v (3H3 'oxy-1-anilide as used in Example 1, 12.2 parts I I of 2-hydroxynaphthalene-3-carboXylic acid- W 1 2'.5-dimethoxy-1'-anilide, there islikewise ob- V r g tained a red tintof very valuable properties as I H CO NH BTY1 to fastness. he dyestuff may be represented by the :formula: i I i 1 CH3 -0H3 2 wherein however the arylradical is free from .I V J any group which renders the dyestufis soluble C1 in an alkaline solution, as, for instance, the I Y sulfonic acid, the carboxylic acid and the hy- OH OCHa droxy group. l I

The following examples serve to illustrate our V invention, but they are not intended to limit I v it thereto, the parts being by weight, unless 8 otherwise stated: H 1 v (1) Cotton material is padded with a groundsubstltutmg the Parts 01 0 ing liquor prepared from 11.1 parts of Z-hydroXys h n a s .80 najphthalene-ZB-carboxylic 1 acid-4'-methoXy-1- m Example 4 part? i anilide, 36 parts by volume of caustic soda solu- 4'bromobenzene" mlddmtg Ted mm 15 qbtamed tion of 34 B, 24. parts of sodium Turkey red of good fastness to l e and weshmg d oil of 50% strength, 500 liters of hot water, the also of a good fastness to hght- T e dyestufi 35 whole being made up with water to 1000 liters. responds Wlth the mu I 1 85 .Ihe dyeing is then developed. with a di'azo-solu- CH3 i tion prepared as follows: 3.1 parts of 1-amino-2.5- I dimethyllchlorobenzene are mixed, while stir- N=N Br ring, with 5.2 litersof hydrochloric acid of 22 '40 B, and some ice-cold water, and to the mixture OH CH: 9 are added 1.44 parts of sodium nitrite dissolved V v v in water. After the diazotization is complete, coNH--00Ha" the mass is made up with cold water to 1000 v liters and neutralized with sodium acetate until i r it shows a neutral reaction towards Congo paper. Since an Object the Present invention S 95- After having been washedand soaped in a boilp v e y fi good fastness r p i 'ing soap bath, the dyeing shows aymiddlingred which dyestuffs areinsoluble in water and al-. tint of very good fastness to chlorine and washkalies, itis to be understood that. the benzene 3 ing, and of a fastness to light,.equa1 to that ever nucleus of the general formula appearing in the obtained with developing dyestuffs. The dyestuff appended claims contains no substituents as are 100,

known to render organic compounds soluble in water or alkaliesand to tend to depreciate the fastness of the dyestuffs to alkalies. Substituents of this kind are, for instance, the sulfonic acid; the carboxylic acid and the hydroxy group.

Werclaim: 1; The compound of the formula:

(1H3 being a red dyestufi of a "very good 'fastness to chlorine and washing and of an excellent fast- 1 V ness to light.

2. The compounds of the general formula:

- I Hal-' I wherein It stands for a radical of the benzene I series, said compounds being dyestuffs of good 30 properties as to fast'ness, and being insoluble in alkaline solutions.

a so

3. The comnound of the formula:

- CH3 7 *J)C Hg being a red dyestuff of 'good fastness properties. 4. The compound of the formula: V

v. C 7 7. a being a red dyestuff of good fastness' to chlorine mandl'ight.

' 5. Fiber dyed with a dyestuff as claimed in claim 1. v 6. Fiber dyed with a dyestuff as claimed in claim 2,

'7. Fiber "dyed, with a dyestuiT as claimed-in claim 3. f j v '8. Fiber dyed with a dyestuff -'as claimed in claim i. V a

- I ERWINcI-IOFFA.

'EUGEN GLIETE BERG; 

